Cyprodinil

Cyprodinil is an anilinopyrimidine broad-spectrum fungicide that inhibits the biosynthesis of methionine in phytopathogenic fungi.¹ It inhibits mycelial cell growth of B. cinerea, P. herpotrichoides, and H. oryzae on amino acid-free media (IC₅₀s = 0.44, 4.8, and 0.03 µM, respectively), an effect that is reversed by addition of methionine or homocysteine. In an MDA-kb2 assay, cyprodinil acts as an androgen receptor (AR) agonist (EC₂₀ = 1.91 µM) in the absence of the AR agonist DHT and inhibits the androgenic effect of DHT (IC₂₀ = 15.1 µM).² It is cytotoxic in a yeast antiandrogen screen (YAS; EC₂₀ = 27.8 µM) but not in an MDA-kb2 assay (EC₂₀ = >50 µM). Cyprodinil increases proliferation of estrogen receptor-expressing BG-1 ovarian cancer cells when used at low micromolar concentrations in combination with 17β-estradiol.³ It also increases tumor mass in a BG-1 ovariectomized mouse xenograft model after 70 days when administered at a dose of 3 mg/kg every three days. Formulations containing cyprodinil have been used in the control of fungi in agriculture.

1.Masner, P., Muster, P., and Schmid, J.Possible methionine biosynthesis inhibition by pyrimidinamine fungicidesPestic. Sci.42(3)163-166(1994) 2.Orton, F., Rosivatz, E., Scholze, M., et al.Widely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogensEnviron. Health Perspect.119(6)794-800(2011) 3.Go, R.-E., Kim, C.-W., and Choi, K.-C.Effect of fenhexamid and cyprodinil on the expression of cell cycle- and metastasis-related genes via an estrogen receptor-dependent pathway in cellular and xenografted ovarian cancer modelsToxicol. Appl. Pharmacol.289(1)48-57(2015)